Ethanol → 2-(Acetylamino)-3-(3,4-dimethylphenyl)propanoic acid

HRID 584221Notes

Reaction equation

HRID 584221 reaction equation
[C:1]([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=1)(C(OCC)=O)[C:6]([O:8]CC)=[O:7])(=[O:3])[CH3:2].[OH-].[K+].C(O)C>O>[C:1]([NH:4][CH:5]([C:6]([OH:8])=[O:7])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 13406779Diethyl 2-acetylamino-2-(3,4-dimethylbenzyl)malonate

Product 1

HCID 27472492-(Acetylamino)-3-(3,4-dimethylphenyl)propanoic acidYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl 2-acetylamino-2-(3,4-dimethylbenzyl)malonate (13.8 g) and potassium hydroxide (2.76 g) were dissolved into a mixed solution of ethanol (138 ml) and water (138 ml) and the solution was stirred under reflux for 8.5 hours. After being cooled to room temperature, the solution was concentrated under reduced pressure and the resulting aqueous solution was adjusted to pH 10 with aqeuous saturated sodium hydrogen carbonate solution. The solution was washed with ethyl acetate and made acidic with diluted hydrochloric acid, and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure to give crystals of N-acetyl-3,4-dimethyl-DL-phenylalanine (5.42 g).

Workup

  1. temperatureunder reflux for 8.5 hours
  2. concentrationthe solution was concentrated under reduced pressure
  3. washThe solution was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-cfecf31e74744b2c93c7ed4c8d823992
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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